We all know Halloween is about the costumes and the drama, but what’s more spooky than a situationship? Those “we’re not really together, but we definitely are” romances have defined entire eras of TV and movies from the Upper East Side penthouses to beach summers, giving us messy breakups, passionate reunions, and way too many “what are we?” conversations, and iconic one-liners that live rent-free in our heads. And, what better way to get real (and real messy) this year than with some situationship Halloween costumes?
So while your friends are busy dressing up as Barbie and Ken for the third year in a row, you can serve something spicier, funnier, fresher, and way more relatable: a situationship costume. These pairs are instantly recognizable, give you an excuse to text your almost-partner, and lean into the fact that modern romance is rarely black and white.
With the undeniably stylish energy of Maddy and Nate from Euphoria to the nostalgia of Ross and Rachel from Friends, these looks let you channel TV’s most iconic “will-they-won’t they” couples without needing to define your own relationship status. Going for something dramatic, playful, or chaotic? I rounded up the ultimate list of Halloween costumes for situationships, because let’s face it: spooky season is messy, and so is love.
- Maddy Perez & Nate Jacobs (Euphoria )
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Maddy’s dramatic and bold makeup makes her instantly recognizable, and pairing her with Nate’s football uniform or a hoodie brings out the toxic but addictive energy. Stylish, chaotic, and perfect for Halloween.
- Belly & Conrad or Belly & Jeremiah (The Summer I Turned Pretty )
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The love triangle that took over social media makes the perfect situationship costume. Belly’s sundresses set the tone, while your partner can lead into Conrad’s moody hoodies or Jeremiah’s bright polos and easy smile.
- Rue & Jules (Euphoria )
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Rue and Jules are the definition of complicated, moving between best friends, lovers, and something in between. Rue’s oversized hoodie and Converse will give her a laid-back vibe, while Jules’s colorful makeup, layered accessories, and bold outfits bring her expressive, dreamy style to life.
- Zoey & Aaron (Growin-ish )
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Zoey and Aaron are the epitome of a college situationship. Zoey’s bold, fashion-girl looks paired with Aaron’s laid-back denim, sneakers, and graphic tees with a cause.
- Issa Dee & Lawrence (Insecure )
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Issa and Lawrence gave us one of the realest situationships on TV. For Halloween, Issa’s bold print or mirror-rap style complements Lawrence’s chill, casual look, making an instantly recognizable pair.
- Carrie Bradshaw & Mr. Big (Sex and the City )
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Carrie and Big are the blueprint for messy TV romance. A tutu or slip dress channels Carrie’s style, while Big’s sleek back suit keeps it timeless.
- Rachel Green & Ross Geller (Friends )
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Rachel and Ross practically invented the phrase “we were on a break.” Rachel can rock a ‘90s slip dress or her Central Perk apron, while Ross leans nerdy with paleontology gear or a dinosaur tee.
- Meredith Grey & Derek Shepard (Grey’s Anatomy )
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MerDer was pure drama, passion, heartbreak, and unforgettable speeches. Scrubs, a lab coat, and maybe a stethoscope are all you need to channel their hospital romance.
- Blair Waldorf & Chuck Bass (Gossip Girl)
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Upper East Side toxicity at its finest. Blair’s headbands, pearls, and preppy skirts meet Chuck’s patterned suits and smug charm. Gossip Girl would 100% blast this messy love life on Halloween night.
- Olivia Pope & President Fitz (Scandal)
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Secret, messy, and political. A tailored white coat, chic heels, and a big glass of red wine would perfectly capture Olivia. And Fitz should lean into his presidential vibe with a navy suit and American flag pin.
- Santana & Brittany (Glee )
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What started as a fling became one of TV’s most beloved queer love stories. Their cheer uniforms are instantly recognizable, with Santana’s sharp attitude and Brittany’s bubbly charm making it unforgettable.
- Devi & Ben (Never Have I Ever )
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The ultimate “enemies-to-lovers” duo, but also maybe still enemies. Devi’s look can be as simple as a bright cardigan and jeans with her signature backpack, while Ben channels his preppy vibe with a button-down and blazer.
- Mindy Lahiri & Danny Castellano (The Mindy Project )
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Mindy and Danny were the definition of flirty one minute and fighting the next. Mindy’s bright, colorful dresses paired with bold accessories show off her personality, while Danny’s button-down and lab coat keep it simple.
- Sam & Ronnie (Jersey Shore )
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If you want pure chaos, this is the one. Sammi’s bodycon dress and hoop earrings, paired with Ronnie’s fitted tee and cargo pants, bring back peak Jersey Shore drama.
- Joey & Dawson (Dawson’s Creek )
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Classic teen-drama angst makes Joey and Dawson a perfect couple for a situationship. Joey’s jeans and a simple tee work effortlessly, while Dawson’s preppy khakis and sweater round it out. It’s low-key look, but people will instantly clock the nostalgia.
- Serena & Dan (Gossip Girl )
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Serena and Dan are the couple that never really made sense, but somehow worked, until it didn’t. Serena’s boho style contrasts with Dan’s flannel or corduroy jacket, which complements his “lonely boy” vibe, making them a recognizable pairing.
- Ezra & Aria (Pretty Little Liars )
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This one is scandalous, and that’s precisely why it works. Aria’s edgy, experimental style, with bold patterns and feather earrings, pairs perfectly with Ezra’s button-downs and teacher blazers. Everyone will recognize, but probably side-eye, it too.
At the end of the day, these couples might be a mess on screen, but they’ll consistently deliver when it comes to costumes, and really, what’s Halloween without a bit of chaos?